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Volumn , Issue 5, 2007, Pages 780-784

Stereoselective access to functionalized dihydrophenanthrenes via reductive cyclization of biaryl ene-aldehydes

Author keywords

Ene aldehyde; Reductive cyclization; Samarium(II) iodide

Indexed keywords

9 ALKYL 10 HYDROXY 9,10 PHENANTHRENE DERIVATIVE; ALDEHYDE DERIVATIVE; PHENANTHRENE DERIVATIVE; SAMARIUM DIIODIDE; UNCLASSIFIED DRUG;

EID: 33947723004     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-970771     Document Type: Article
Times cited : (13)

References (35)
  • 5
    • 0028230211 scopus 로고
    • For compound 4, see
    • (e) For compound 4, see: Zheng, G.; Ho, D. K. J. Nat. Prod. 1994, 57, 32.
    • (1994) J. Nat. Prod , vol.57 , pp. 32
    • Zheng, G.1    Ho, D.K.2
  • 18
    • 33947728173 scopus 로고    scopus 로고
    • Although a mixture of dl- and meso-isomers of 2,4-pentanediol was employed, the latter preferentially took part in the reaction, giving the diastereomer 12 in 81% yield with a small amount of other diastereomers (<6% yields, The structure of 12 was assigned by 1H NMR and diagnostic NOE interactions Figure 2
    • 1H NMR and diagnostic NOE interactions (Figure 2).
  • 19
    • 33947729419 scopus 로고    scopus 로고
    • This reaction also proceeded in the absence of a proton source, giving the product in 10% yield with a sizable amount of unidentified byproducts
    • This reaction also proceeded in the absence of a proton source, giving the product in 10% yield with a sizable amount of unidentified byproducts.
  • 20
    • 33947722195 scopus 로고    scopus 로고
    • 254) to give 7a (trans/cis = 10:1) in quantitative yield as a colorless oil.
    • 254) to give 7a (trans/cis = 10:1) in quantitative yield as a colorless oil.
  • 25
    • 33947732063 scopus 로고    scopus 로고
    • Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994, Chap. 14-15.
    • (d) Eliel, E. L.; Wilen, S. H. Stereochemistry of Organic Compounds; Wiley: New York, 1994, Chap. 14-15.
  • 27
    • 33947723455 scopus 로고    scopus 로고
    • c in 17 suggested the conformation shown below (Figure 3). (Chemical Equation Presented)
    • c in 17 suggested the conformation shown below (Figure 3). (Chemical Equation Presented)
  • 28
    • 33947721964 scopus 로고    scopus 로고
    • Compound 16 was conformationally stable at room temperature. However, it underwent isomerization in toluene in 5 h at 90°C. The equilibrium ratio was 36:64, diequatorial/diaxial (Figure 4). (Chemical Equation Presented)
    • Compound 16 was conformationally stable at room temperature. However, it underwent isomerization in toluene in 5 h at 90°C. The equilibrium ratio was 36:64, diequatorial/diaxial (Figure 4). (Chemical Equation Presented)
  • 29
    • 33947723571 scopus 로고    scopus 로고
    • The stereostructure of trans-7b was determined by X-ray crystal structure analysis (Figure 5). (Chemical Equation Presented)
    • The stereostructure of trans-7b was determined by X-ray crystal structure analysis (Figure 5). (Chemical Equation Presented)
  • 30
    • 33947730645 scopus 로고    scopus 로고
    • The PTLC purification gave four separable diastereomers associated with relation between the 9,10-stereogenic centers in the phenanthrene skeleton and the sulfur chiral center. Oxidation of trans-7c and trans-7c′ by MCPBA led to the same compound 18. The stereostructure of 18 was determined by X-ray analysis (Scheme 9). In a similar manner, cis isomers of 7c and 7c′ were both converted into cis-19.
    • The PTLC purification gave four separable diastereomers associated with relation between the 9,10-stereogenic centers in the phenanthrene skeleton and the sulfur chiral center. Oxidation of trans-7c and trans-7c′ by MCPBA led to the same compound 18. The stereostructure of 18 was determined by X-ray analysis (Scheme 9). In a similar manner, cis isomers of 7c and 7c′ were both converted into cis-19.
  • 34
    • 33947727815 scopus 로고    scopus 로고
    • Isolation of the Pummerer product was attempted; however, it was prone to undergo hydrolysis to form the corresponding aldehyde. This aldehyde was easily dehydrated to afford 9-phenanthrene carboxaldehyde.
    • Isolation of the Pummerer product was attempted; however, it was prone to undergo hydrolysis to form the corresponding aldehyde. This aldehyde was easily dehydrated to afford 9-phenanthrene carboxaldehyde.
  • 35
    • 33847086035 scopus 로고    scopus 로고
    • 2 in THF, see: Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693.
    • 2 in THF, see: Girard, P.; Namy, J. L.; Kagan, H. B. J. Am. Chem. Soc. 1980, 102, 2693.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.